Tuscany via car

What locations? Where do you want to go? It is easier to move around with a car, but I am still more inclined to stay 7 nights in 2 locations and do day trips.

Made this difficult choice ourselves last year. We spent 3 nights Siena, 3 nights Montalcino, 2 nights Orvieto, and it was a wonderful introduction to Tuscany. We spent one day without a car in Siena taking an escorted tour. Then we rented a car which we kept until Orvieto so we could daytrip both from Siena and Montalcino. This agenda let us experience two entirely different types of Tuscan environs: Siena a small city with easy access to towns like Volterra and San Gimignano, and Montalcino a small town with access to wine country, abbeys, and hiking. Orvieto was a stop on the way to Rome which was yet another completely different "scene."

Depends on how much you hate packing and unpacking.
Also depends on the extent to which you want to be able to experience different towns in the evening. If this is your first time in Italy, I would suggest a hybrid - spend 2-3 nights each in 5 different places. And forget the car. Buon viaggio.

Minimize the number of times you have to pack up, check out and move to a new hotel. The best thing about having a car is that you can do a lot of great day trips in Tuscany from one place. Also, if you have a car, consider staying in a very small town or an agrituturismo. Parking is easier, as is getting into and out of where you are staying. I have a great place to stay in Lucca, but it takes about 15 minutes to get out of town and on the road to where I want to go.

"Next time" we will do as Doug suggests and stay in one place. (In fact we are doing 6 nights in Umbria this year, no car, taking trains and busses to day trip.) However I would not have done my first trip to Tuscany any other way. It was great to experience after-dark in more than one town. Loved taking a stroll after dinner, stopping for un caffe. Remember if you have to drive "home" after dinner you will not be able to drink with dinner. Downside of the agriturismo.

Yes, Laurel points out the downside of my suggestion. However, we once stayed at an agriturismo north of Siena that had its own excellent restaurant and a separate bar that was the local hangout!

One place you might consider staying is Fiesole, located on the hill overlooking Florence. It has a lovely village feel to it. It has some nice places to stay, lovely vistas of Florence and the countryside, and some good restaurants. It has free parking in some areas. You can catch the bus down to the heart of Florence from Fiesole. You can also drive through the countryside north of Florence where few tourists venture.

I would agree that you should stay in two locations and take day trips to explore. This will give you more time to explore if you don't have to pack up and leave every other night. Especially if you have a car, getting around Tuscany and seeing some of the small cities will be fairly easy.

I will give the other side. I dont like staying at one place and daytripping because then every place I go I am one of the crowd of daytrippers.Most towns are crowded during the day and then in the evening and early morning become much nicer places to visit.I would rather arrive at a town in mid afternoon and stay the night and then go to another town the next day staying one night or possibly two.I understand it is nice to pack and unpack less often.

Agree with Jack, especially if it is smaller towns like in Tuscany... I have done both, but do not regret my first trips in seeing everything I could cram in....with a car, its easy. Pack light and repacking is not really an issue...ten minutes and you should be good to go. And yes, assume you will want to return. But, for some people life happens and their dreams of returning don't work out. So, see what you can and enjoy it all. Pick your favorites and dream of your return! and , if you can, make it happen. Two nites stays have been plenty for me at lots of locations.